Orange vat dyestuffs and process of making same.



- STATES PATENT OFFIGE.

GADIENT' ENGI AND JAROSLAV FRfiHLICH, OF BASEL, SWITZERLAND, ASSIGNORS Ti) SOCIETY OF CHEMICAL INDUSTRY IN BASLE, OF BASEL, SWITZERLAND.

ORANGE VAT DYESTUFFS AND PROCESS OF MAKING SAME.

Tl,8l,898.

Ho Drawing.

To all whom it may concern:

Be it known that we, GADIENT ENGI,- doctor of philosophy and chemist, a citizen of the Swiss Republic, and resident of'Basel Switzerland, and JAROSLAV FRoHLIcIi', doctor of philosophy and chemist, a subject of the Emperor of Austria-Hungary, and resident of Basel, Switzerland, have invented new and useful Orange Vat Dyestuifs and a Processof Making Same, of which the following is a. full, clear, and exact specification.

WVe have found, that valuable new orange dyestuffs are obtained, by acting with a halogenating agent on the condensation product of an acenaphthenequinone com-. pound with an am1no-oxythionaphthene.P

but dissolving in concentrated sulfuric acid with a blue color.

The invention is illustrated by the following examples, the parts being by weight.

' Example I: In a mixture of 80 parts of.

sulfuric acid of 97 per. cent. and 7 parts of broniin, cooled to 0 C. are introduced while stirring 3,4 parts of the product resulting from the condensation of acenaphthenequinonc of the structural formula tic-co l I l with 6-amino-3-oxy-l-thionaphthene of the structural formula Specification of Letters Patent.

Application filed October 19, 1911.

They form in dry state brownish I Patented Dec. il d, ii 'idlib'i.

Serial No. 655,498.

in alcohol the said condensation product corresponding to the structural formula The temperature is then raised in the course of 4 to 5 hours to 20-25 and the mixture stirred at this temperature for about hours. The mass is then poured into watery:

the whole filtered and the solid matter washed until the washings are neutral.

The dried dyestufi' constitutes a brown powder dissolving in concentrated sulfuric acid with a blue color. In an alkaline vatit dyes cotton and wool vivid orange tints.

Example II: 3,7 parts of the product resulting from the condensation of the 6- amino 3-oxy 1 thionaphthene carboxylic' acid corresponding to the formula with acenaphthene-quinone in acetic anhy drid are suspended in 35 to 40 parts of nitrobenzene and into this mixture are introduced 7 parts of bromin, the mixture being hereafter stirred for 12 hours at the ordinary temperature. The mass is then heated for 1 to 2 hours at 200220 (1, cooled down and filtered in order to separate the brominated product. The new dyestufi is ob tained in form of a brownish yellow powder dissolving in concentrated sulfuric acid with a greenish blue color. In an alkaline vat it dyes animal and vegetable fibers brownish orange.

In an analogous manner dyestuii's are obtained when the condensation products de rived from the substitution products of are naphthene-quinone,'as for instance Chloracw naphthene-quinone, bromacenaphthene-quinone, amino-accnaphtheue-quinone, are cuployed as parent material.

Instead of the diluents used in the exam ples, other suitable solvents or diluents may be used, such. as for example chlorosulton'ic acid and sulfuryl chlorid. The broniination can also be etl'ected directly with liquid bromin Without employ of a diluent. Finally chlorin may be employed as halogenating agent.

, What We claim is:

1. The herein described processfor the manufacture of orange vat dyestufi's, which consists in acting with a vhalogenating agent on a condensation product obtainable by condensing an acenaphthene-quinone compound with an amino-oxythionaphthene.

2. The herein described process for the manufacture of orange vat dyestufl's consisting ineacting with a halogenating agent on a condensation product obtainable by heating an acenaphthenc-quinone compound with an a1nino-oxythionaphthenc-carboxylic acid this latter being intermediat'ely transformed into the corresponding amino-oxythionaphthene which reacts upon the acenaphthene-quinone compound.

3. The herein described process for the manufacture of orange vat dyestufi's by treating with bromin. the condensation products obtainable by condensing acenaphthenequinone with an amino-oxythionaphthcne.

4-. The herein described process for the manufacture of orange vat dyestufls by treating with broinin thecondensation products obtainable by heating acenaphthenequinone with an amino-oxythionaphthenecarboxylic acid, this latter being intermediately transfori'ned into the corresponding an'nno-oxythionaphthene which reacts upon the acenaphthene-quinone compound.

5. As new products the orange vat dyestufl's obtainable by acting with a halogenating agent on a condensation product derived from an acenaphthenequinone compound and (S-aniino-oxythionaphthene the said vat dyestuffs forming in dry state brownish yellow to brown powders insoluble in water, dissolving inconcentrated sulfuric acid with a blue color and dyeing vegetable and animal fibers in an alkaline vat orange to brownish orange shades. i i

6. As new products the orange vat dyestuffs obtainable by acting with bromin on the condensation products corresponding to the formula derived from acenaphthene-quinone and 6- amino-oxythionaphthene, forming in dry' state brownto brownish yellow powders in soluble in water; dissolving in concentrated sulfuric acid with a blue colorand yielding .with alkaline reducing agents violetish brown vats dyeing vegetable and animal fibers orange shades.

In witness whereof We have hereunto- GADIENT ENGI. JAROSLAV rnonLion.

\Vitnesses Gnoncn Grrrono, AMAND BRAUN. 

